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Queer Authenticity, Caravaggio, and the Lesbian Witches of Karen & the Sorrows

by Rachel Cholst

Karen & The Sorrows - Guaranteed Broken Heart album cover painted by Amanda Kirkhuff
Karen & the Sorrows album painting by Amanda Kirkhuff

Country music, if nothing else, has a deep sense of its history. This nostalgic bent for the past helps preserve incredible traditions, but it also gives the genre an inherent conservatism. It’s also a history shaped by what was commercially palatable in the latter half of the 20th century — which means that many voices were either sanitized or left out altogether. On Karen and the Sorrows Guaranteed Broken Heart, Karen Pittleman carefully wove elements of queer history into the country album, asserting queer people’s place in country music.

Karen & the Sorrows – When People Show You Who They Are

On Guaranteed Broken Heart, few of the lyrics are explicitly queer. Instead, Pittleman firmly centered the album’s queerness in its most public-facing aspects: the album’s cover and the three music videos that have been released for the song “Guaranteed Broken Heart” and “Why Won’t You Come Back to Me.”

I caught up with Amanda Kirkhuff, who painted the album cover, a stunning portrait of Pittleman that imbues her with a fierce confidence, the fury of a woman scorned, and an undeniable eroticism. In the portrait, Pittleman is surrounded by flowers and other objects that carry deep significance for queer history.

“When Karen initially contacted me about doing the cover for Guaranteed Broken Heart, she was very open about ideas and we discussed keeping the imagery within my oeuvre. Since my paintings can be Caravaggiesque, we decided to riff on Caravaggio’s very homoerotic “Boy with a Basket of Fruit.

Carvaggio’s ‘Boy With a Basket of Fruit’


We choose the bouquet she holds very carefully, all of the objects have queer symbolism,” Kirkhuff writes. “We traded images back and forth, talked on the phone while at the dollar store, and shopped online for the right props. What we finally chose is a hanky code reference (hunter green and grey, I’ll let the readers do their homework about what those mean,) plus pansies, violets, lavender roses, and green carnations. The green carnations were a new discovery for me! Apparently, Oscar Wilde proliferated them as a queer symbol in 1892.”

Karen & the Sorrows – Why Won’t You Come Back to Me

In the video for “Why Won’t You Come Back to Me,” the first video released for the album, Pittleman dug deeper into the past. AJ Lewis, former Karen and the Sorrows bassist and Assistant Professor of Gender, Women’s, and Sexuality Studies at Grinnell College, elaborated on the fundamental connection between queer identities and witchiness. While there are more direct connections between queer folks distancing themselves from Judeo-Christian religions, Lewis points to the individual agency centered by these practices. “One of the things that’s interesting to me about witchcraft and queers is that it can be a way of claiming alternative forms of agency and powers to act upon the world around us.”

This is especially true in the video. “[Karen] is talking about a breakup and she’s in this disempowered state, right? The video has her making a spell right as a strategy for influencing a situation.”

Lewis also observes that there is a direct link between the postwar adoption of neo-paganism in the United States and activism — particularly the Women’s International Terrorist Conspiracy from Hell (WITCH.)

Women’s International Terrorist Conspiracy from Hell (WITCH)


If you’re reading this, you already know that astrology and witchcraft have made a resurgence in millenial and Gen-Z queer culture. Lewis ascribes it to a form of separatism: “We’re actually bombarded with more and more and more public visibility around LGBT issues in really mainstreaming and like normalizing ways. Gay public representation has honestly become like so boring, you know? It’s like, ‘I’m not like those white picket fence gays.’”

Karen & the Sorrows – Guaranteed Broken Heart

In “Guaranteed Broken Heart,” Pittleman re-stages a New York City tradition that unabashedly pushed against that conformity. In the video, Pittleman and a number of other sad souls compete in a Miss Broken Heart competition, emceed by legendary drag king Murray Hill. The contest is based on the Mis Lez pageant, which took place (based on my Googling) from 2006 – 2013.

“My theme was ‘Do Ask, Do Tell,’” recalls actress and Miss Lez 2010 winner Drae Campbell. Each contestant had to be sponsored by a local party or establishment. Since Campbell was sponsored by Rebel Cupcake, a queer cabaret show, she had to ensure that she repped them. “I pulled a camo cupcake out of my G-string,” she laughs. Needless to say, Campbell won.

Campbell plays the judge in “Guaranteed Broken Heart” and recalled the experience fondly. “We had a lot of laughs. We had a good time. Karen was calling all the shots and she was doing it in this really sweet, kind, generous way. She looks gorgeous. It’s only like in the last couple of years that I’ve been working with a lot of like queer people, trans people, women. It was such a great feeling to be like, that’s the person in charge, bitches!”

Like Lewis, Campbell mused on the sense of conformity prevalent in the queer community today. The Miss Lez pageant celebrated queer life on the Lower East Side (and, as the community got priced out of the neighborhood, Williamsburg.) “This thing is happening now where it’s cool for everybody to be queer and it’s being commodified and we’re becoming these exploitable commodities. It would be nice to have the old school, dirty, downtown queerness crowd.”

When Hill made a casual remark on set about reviving the pageant, Campbell reports that the cast and crew enthusiastically supported the idea. “It’s so fun. It’s so insane. The kids need it.”

Now that Karen and the Sorrows are on tour to support “Guaranteed Broken Heart,” they’re creating that sense of campy rebelliousness wherever they go. Whether you’re a witchy queer or prefer a white picket fence, that authenticity binds us to our past and paves the way to our future.